A week of Puerto Rico highlights

In April 2019 I invited a few close friends to Puerto Rico for my birthday. I figured 5-10 would show up. Instead several brought friends and we ended up having a 51 person week long party / unconference / exploration of Puerto Rico.

There were wild horses, bioluminescent bays, giant telescopes, and discussions that made me feel lucky to have such weird and wonderful friends. It was also astonishingly easy to put together, which shows how ready Puerto Rico is for more tourists.

If you’re looking for a very fun vacation that supports many local entrepreneurs and Puerto Rico’s ongoing recovery, follow the itinerary below.

Wednesday in Old San Juan: paella, piano, and dancing

Old San Juan is one of the oldest settlements in the Americas, with buildings dating back to the 16th century. It feels more European than anywhere else I’ve been in the ‘new world’.

Most of these photos are by Daniel Gaspersz, Tammie Kim, Matthew Brown, and Lena Xiao, but I’m afraid I don’t remember which are which. Thanks to all of them!

We rented a 200 year old house constructed by rum baron, now owned by my friend Jon. He rents it on Airbnb here.

We watched sun set from the highest point in Old San Juan: the roof of the Gallery Inn, a fabulous boutique hotel full of art and parrots (there are five: an African Grey, two macaws, and two cockatoos). The hotel is a labor of love created by the 80-something Jan D’Esopo, a gifted painter.

We hired Jorge Morales, the chef from Cafe Poesia, an arts-focused cafe in Old San Juan, to make paella live. If you don’t want to hire him for an event, you can enjoy his paella of the week at Cafe Poesia every Friday at lunchtime.

We ended the night at my favorite one-two punch in Old San Juan: the Cannon Club at the Gallery Inn and La Factoria.

Cannon Club is a gathering place of colorful people, parrots (the same ones from the hotel above) and pianos. Gifted artists often show up unannounced to play live; Alicia Keys and Yo-Yo Ma were both here earlier this year.

La Factoria is a James Beard Award-winning cocktail bar that is actually a labyrinthine collection of 6 bars accessed speakeasy-style through unmarked doors. From the cocktail bar you pass through to a wine bar, a salsa/dancing space that often has live music, a dungeon-like disco with an even more dungeon-like cocktail bar in the very back, and another bar I don’t want to describe in too much detail because it’s more fun to bring people there in person. Since this was my actual birthday, someone was nice enough to arrange a cake and buy me way too many shots.

Thursday: beach day in San Juan / exploring art and nightlife in Santurce

Early risers spent the morning visiting El Morro, a monumental fort built by the Spanish over the 16th-19th centuries at the edge of Old San Juan.

We spent the afternoon at Ocean Park beach, surely one the of the best beaches in the world. A few friends bonded with the local kitesurfing crew while most of the rest of us played volleyball.

By late afternoon we migrated to Calle Cerra in the Santurce neighborhood, a mecca for local art where many of the buildings are covered in murals.

We started with dinner at El Patio de Sole, a restaurant that looks like the inside of a well-curated thrift store. It serves good old fashioned Puerto Rican comfort food.

We visited my friend Shipwreck’s studio, sadly now closed while he works on finding a new live/work space. This was the first, though certainly not the last, time Sean somehow ended up shirtless.

Thursday nights on Calle Cerra usually see a number of gallery openings and live bomba y plena music at Esquina el Watusi, a favorite local bar.

There was much dancing on the street. For no good reason, a number of us decided to wear cheetah print.

The most energetic of the group ended up at El Local. After Hurricane Maria, this alt bar became a soup kitchen and shelter for many in the neighborhood. When we went it was the weekly LGBTQI night, complete with fire dancing performances.

Friday: Space telescopes + ancient petroglyphs

We had a leisurely morning before taking a bus to Arecibo Observatory. It was until 2014 the largest space telescope in the world (now the Chinese have built a bigger one).

The telescope is in a crater in the middle of a mountain range. We had to turn off our cell phones so as to not interfere with the telescope *talking with space*. The accompanying museum had fun interactive exhibits explaining the telescope’s importance to our space program.

Next we headed to the nearby Cueva del Indio, a spectacular beach/rock formation where there the Taino native Americans carved petroglyphs into the cave walls about a thousand years ago.

You have to climb down a bit to see the petroglyphs. I was too distracted by the scenery so missed them. Good thing I live here and can go back..

A few people got their drone one.

And watched the sun set while eating freshly caught seafood from the nearby Salitre Meson Costero.

Saturday: to the (other) island!

Off the eastern coast of Puerto Rico lies the perfect tropical island of Vieques. Once used as a military training site, the island is turning into an eco-tourism paradise powered almost entirely by renewable energy. We took a bus from San Juan to Ceiba where we caught the ferry over.

When I say perfect tropical island, I mean pristine turquoise water, palm trees, and… wild horses!

And foals.

Some people stayed in hotels and Airbnbs, but the majority of the group camped on Sun Bay Beach, which had showers and toilets (though BYO toilet paper).

We worked with the excellent Banquetealo to have food catered to the beach.

We rented jeeps and golf carts to get around. Esperanza is the main town on the side of the island with the bioluminescent bay, which was our target for the evening.

What? You didn’t know the brightest bioluminescent bay in the world is in Puerto Rico? A place where you put your hand in the water and millions of microscopic organisms fluoresce so your hand is covered in blue sparkles? Unfortunately its’ basically impossible to capture on camera so instead I’ll share pictures of our campsite.

It’s easiest to appreciate the bioluminescence under a new moon so it’s as dark as possible. Which means we also got to appreciate the stars!

Sunday: back to San Juan and beyond

Some of us made it to sunrise. Others did not.

Then it was back to San Juan via ferry and bus (some people flew – there are 15 min flights into SJU and Isla Grande, a smaller municipal airport in San Juan). We finished the weekend with a low key barbecue at a friend’s house.

For transport, I worked with chartercoachpr.com who were excellent. We hired Abe’s Bio Bay Tours on Vieques to visit Mosquito Bay. Banquetealo helped cater our dinner on Vieques. Other than a few dinner reservations, we figured out everything else along the way. I couldn’t have pulled this together without everyone stepping up to figure out the many tiny things that needed doing, and owe a huge thanks to everyone who came and made the experience so perfect. But even if you don’t have my friends with you, Puerto Rico has its own magic: come and see for yourself.

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I’ve moved to Puerto Rico!

What the title says!

I don’t know how long I’ll stay, because everything about this place is new to me. I visited for the first time in January and made the decision to move in February. But I am more excited about Puerto Rico than any place I’ve been in years and could envision building a long-term home here. Here are some of the reasons why.

First, a quick note about the basics: as the CEO of a distributed team at Hitlist, my priority is to live in a place where there is reliable internet, easy-to-navigate bureaucracy, excellent travel connections, and quality of life. To the first three: I get minimum 25mbps internet up and down most places, my coworking space scans/forwards my mail as needed, and there are flights to 47 destinations in 15 countries from an airport that is 15 minutes away from the city center. As for quality of life:

  • Puerto Rico is full of smart weirdos. It’s got a reputation as a haven for crypto bros, and a few outlandish ones give the place a bad rap. In the majority of cases, though, people who are really into crypto/blockchain technology are also radical thinkers who I find quite enjoyable, and some of the leaders in the field are here. Beyond that,
  • It’s diverse. Puerto Rico is a melting pot of Latin, African, native American, European, and Asian influence. I’ve not encountered a single unfriendly person, and social circles tend to feature a mix of ages, colors, backgrounds, and professions – something I sorely missed in San Francisco. People even have children here! No one I socialized with in SF had children (except for Avi, if you’re reading this, hi!)
  • Art is everywhere. Every shop, office, and home is filled with art. Not the kind that you get from IKEA or Society6, but things that individual people make. In my first two weeks I met more artists creating amazing stuff (including emerging art with VR/AR and electronic music) than I met in three years in San Francisco. As a bonus, the art that’s being created here is not primarily geared towards being destroyed at Burning Man every year.
  • It’s warm, but not too warm. It’s consistently in the 70s-80s year round (I’ve been told the summer humidity is tough; I don’t tend to mind that but will have to report back after I’ve experienced it).
  • I get to practice my Spanish, though I don’t strictly need to since most people speak English. Charlemagne said ‘to learn another language is to have another soul’ and since at least one of my souls is going to hell it would be useful to have a backup.
  • It’s affordable. You can rent a basic apartment on/near the beach for $500-600/month. You can bike everywhere you probably want to go, or rent a car for $30/day if you want to explore the island.
  • People take wellness seriously, and are pushing the boundaries of conventional medicine. Social life is highly physical: volleyball, acroyoga, salsa dancing, hiking, beach tennis, and climbing are part of a normal week. I’ve been learning to juggle (a skill I never knew I wanted, but am enjoying) at a weekly ‘circus jam’ in a 500 year old former army barracks. There are a lot of people working thoughtfully on ‘nature’s medicine’ (read: natural alternatives to pharmaceuticals, including marijuana, mushrooms, ayahuasca, etc) both legally and semi-legally. Puerto Rico’s status as a territory but not a state leads to some grey areas that are useful as scientists attempt to do studies to determine what the health benefits really are (or are not). I’m bullish on that sector as the US healthcare system gets closer to breaking and societal acceptance of alternative medicine shoots up. Puerto Rico is already the ~5th largest hub for pharma R&D worldwide so there’s a lot of infrastructure in place to scale new ideas.
  • The food! Ripe mangoes and avocados fall from trees. It’s easy to eat organic and local. I’ve lost ten pounds without thinking about it.
  • The nature! If surfing perfect turquoise waves isn’t your thing, you can hike lush jungles to hidden waterfalls, swim in bays full of bioluminescent plankton (the brightest in the world), and/or snorkel over colorful tropical reefs.
  • This is a unique inflection point in PR’s history. Something like $30bn of federal aid has been earmarked for reconstructing Puerto Rico post hurricanes Irma and Maria. The island needs smart, innovative people to bid on the massive contracts that are coming up, in pretty much every sector – urban revitalisation, healthcare, infrastructure, etc. There are already some savvy early movers here and I think many more will come as the extent of opportunity here becomes better known.

All in all, it feels on the ‘fringe’ in a good way, like Istanbul did when I moved there in 2009. Then you have all the conveniences of still being in the US: no telecoms roaming, no additional charges on shipping or moving money (after many years of living abroad, being able to order things off Amazon Prime really is a joy). Plus there are 12 direct flights to NYC a day – I can leave here in the morning and be at a lunch meeting in Manhattan if need be.

It’ll be interesting to revisit this in a few years and see how well some of my first impressions weather. But for now, I’ll leave you with this image of my new machete and me.

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